Patent GB-634183-A (GB)
Title: Esters of polyoxyalkylene diols and methods of making such esters
IPC: C10M105/34
Filed: 1947-01-31
Abstract: Esters of mixtures of polyoxyalkylene glycols containing both the oxyethylene radical and the oxy 1, 2-propylene radical in a ratio from 1/3 -9 parts by weight of 1, 2-propylene oxide for each part of ethylene oxide, said mixture having an average molecular weight of at least 300 attributable to the oxyethylene and oxypropylene radicals, are prepared by esterifying said glycols with an aliphatic acylating agent such as a fatty acid, anhydride or acyl chloride.  Esters with lower fatty acids such as acetic to butyric have lower viscosities than the initial glycols and are useful as metal lubricants.  Figures are given showing how the rate of change of viscosity with temperature varies with the different esters and with the ratio of ethylene to propylene oxide in the glycols.ALSO:Esters of mixtures of polyoxyalkylene glycols containing both the oxyethylene radical and the oxy 1,2-propylene radical in a ratio from 1/3 -9 parts by weight of 1,2-propylene oxide for each part of ethylene oxide, said mixture having an average molecular weight of at least 300 attributable to the oxyethylene and oxypropylene radicals, are prepared by esterifying said glycols with an aliphatic acylating agent such as a fatty acid, anhydride or acyl chloride.  The glycols may be obtained as described in Specifications 610,505 and 651,712 and esterified by heating in presence of a mineral acid and under reduced pressure. The esters with higher fatty acids such as stearic are good emulsifying agents and may be used for forming water dispersions of 2-ethylhexandiol-1,3, for rendering cloth insect repellent, or of dimethyl phthalate.  Esters with lower fatty acids such as acetic to butyric have lower viscosities than the initial glycols and are useful as metal lubricants.  Figures are given showing how the rate of change of viscosity with temperature varies with the different esters and with the ratio of ethylene to propylene oxide in the glycols.  By using less than two moles. of fatty acid per mole. of glycol, partial esters are produced.  With the more volatile acids such as butyric, 2-ethylbutyric and 2-ethylhexanoic, it is preferred to use an entrainer, e.g. a water-immiscible liquid such as benzene or di-isopropyl ether.  In examples, distearates, dibutyrates, di-(2-ethylchexanates), and a partial stearate ester of glycols having oxide ratios varying from 10 : 90 to 75 : 25 are prepared.ALSO:Esters of mixtures of polyoxyalkylene glycols containing both the oxyalkylene radical and the oxy-1,2-propylene radical in a ratio from 1/3 -9 parts by weight of 1,2-propylene oxide for each part of ethylene oxide, said mixture having an average molecular weight of at least 300 attributable to the oxyethylene and oxypropylene radicals, are prepared by esterifying said glycols with an aliphatic acylating agent such as a fatty acid, anhydride or acyl chloride.  The glycols may be obtained as described in Specifications 610,505 and 651,712 and esterified by heating in presence of a mineral acid and under reduced pressure. The esters with higher fatty acids such as stearic are good emulsifying agents and may be used for forming water dispersions of 2-ethylhexanediol-1,3, for rendering cloth insect-repellant, or of dimethyl phthalate.  Esters with lower fatty acids such as acetic to butyric have lower viscosities than the initial glycols and are useful as metal lubricants.  Figures are given showing how the rate of change of viscosity with temperature varies with the different esters and with the ratio of ethylene to propylene oxide in the glycols.  By using less than 2 moles. of fatty acid per mole. of glycol, partial esters are produced.  With the more volatile acids such as butyric, 2-ethylbutyric, and 2-ethylhexanoic, it is preferred to use an entrainer, e.g. a water-immiscible liquid such as benzene or di-isopropyl ether. In examples, distearates, dibutyrates, di(2-ethylhexanates), and a partial stearate ester of glycols having oxide ratios 10 : 90 to 75 : 25 are prepared.ALSO:Aqueous dispersions of the insect repellents 2-ethylhexandiol-1, 3 or dimethyl phthalate are prepared by using as emulsifying agents esters of mixtures of polyoxyalkylene glycols containing both the oxyethylene radical and the oxy 1, 2-propylene radical in a ratio from 1/3-9 parts by weight of 1, 2-propylene oxide for each part of ethylene oxide, said mixture having an average molecular weight of at least 300 attributable to the oxyethylene and oxypropylene radicals, and prepared by esterifying said glycols with a higher fatty acid (e.g., stearic acid) or its anhydride or chloride.